Pericyclic monosubstituted amphiphilic phthalocyanine photosensitive agent as well as preparation and application thereof

A single-substituted, substituted group technology, applied in the field of photodynamic drug or photosensitizer preparation, can solve the problems of poor biological selectivity, unstable composition, high skin phototoxicity, etc., and achieve a reasonable and feasible preparation route, molar absorption coefficient The effect of large, easily available synthetic raw materials

Active Publication Date: 2019-03-12
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Hematoporphyrin derivatives have shown certain curative effects, but also exposed serious disadvantages: the maximum absorption wavelength (380-420nm) is not in the red light region (650-800nm) with better transmittance to human tissue, and the skin has high phototoxicity. It is a mixture and its composition is unstable, so its clinical application is limited, so the development of a new generation of photodynamic drugs (photosensitizers) is an international research hotspot
However, currently reported biologically active phthalocyanine complexes still have deficiencies, such as lack of amphiphilicity, poor stability, complex synthetic routes, or poor bioselectivity, etc., which need further improvement.

Method used

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  • Pericyclic monosubstituted amphiphilic phthalocyanine photosensitive agent as well as preparation and application thereof
  • Pericyclic monosubstituted amphiphilic phthalocyanine photosensitive agent as well as preparation and application thereof
  • Pericyclic monosubstituted amphiphilic phthalocyanine photosensitive agent as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis and Physicochemical Properties of 1-(4-Sodium Sulfonate-Phenoxy) Phthalocyanine Zinc

[0041] ,

[0042] Formula 1)

[0043] This compound can also be called α-(4-sodium sulfonate-phenoxy)zinc phthalocyanine, and its structure is shown in formula (1), wherein:

[0044] .

[0045] (1) Preparation of 3-(4-sulfonic acid-phenoxy) phthalonitrile sodium salt: 3-nitrophthalonitrile (5mmol) and 4-hydroxybenzenesulfonate sodium (5~7.5mmol, Preferably 5mmol) as the reactant, dimethyl sulfoxide (10~25mL, preferably 10mL) as the solvent, in the presence of potassium carbonate (7.5~15mmol, preferably 10mmol, added in three batches) and nitrogen protection, room temperature~45°C Stir the reaction at 45°C (preferably 45°C) for 48-96 hours, monitor by thin-layer chromatography, and terminate the reaction when 3-nitrophthalonitrile is basically consumed. Filter the reaction mixture with a microporous organic membrane, collect the filtrate, then add the filtrate to 100m...

Embodiment 2

[0050] Synthesis and Physicochemical Properties of 1-(6,8-Potassium Disulfonate-2-Naphthyloxy) Phthalocyanine Zinc

[0051] ,

[0052] Formula 1)

[0053] This compound can also be called α-(6,8-disulfonic acid potassium-2-naphthyloxy)zinc phthalocyanine, and its structure is shown in formula (1), wherein:

[0054] .

[0055](1) Preparation of 3-(6,8-disulfonic acid-2-naphthyloxy) phthalonitrile dipotassium salt: with 3-nitrophthalonitrile (5 mmol) and 2-naphthol-6, Dipotassium 8-disulfonate (5~7.5mmol, preferably 5mmol) was used as reactant, dimethyl sulfoxide (10~25mL, preferably 10mL) was used as solvent, in potassium carbonate (7.5~15mmol, preferably 10mmol), divided into three In the presence of batch addition) and nitrogen protection, the reaction was stirred at room temperature to 45°C (preferably 45°C) for 48 to 96 hours, monitored by thin-layer chromatography, and the reaction was terminated when 3-nitrophthalonitrile was basically consumed. Filter the reactio...

Embodiment 3

[0060] Synthesis and Physicochemical Properties of 2-(4-Sodium Sulfonate-Phenoxy) Phthalocyanine Zinc

[0061] Replace the 3-nitrophthalonitrile in Example 1 with equimolar 4-nitrophthalonitrile to obtain the corresponding peripheral monosubstituted phthalocyanine metal complex, i.e. β-(4-sulfonic acid Sodium-phenoxy)zinc phthalocyanine. The structure of the obtained product is the same as that of the phthalocyanine product described in Example 1, except that the position of the substituent is replaced by the β position.

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Abstract

The invention discloses a pericyclic monosubstituted amphiphilic phthalocyanine photosensitive agent as well as preparation and application thereof, which belongs to the field of preparation of photodynamic drugs or photosensitive agents. A compound of the invention has the characteristics that the amphipathy is realized, the structure is clear, nano particles which can be assembled into a quenching state in a physiological solution is realized, but the nano particles can be activated by albumin, and the pericyclic monosubstituted amphiphilic phthalocyanine photosensitive agent is an activatable targeting photosensitive agent.

Description

technical field [0001] The invention belongs to the field of preparation of photodynamic drugs or photosensitizers, and in particular relates to a pericyclic monosubstituted amphiphilic phthalocyanine photosensitizer and its preparation and application. Background technique [0002] Phthalocyanine complexes are an important class of functional materials, and have important applications in the fields of dyes, optical recording media, nonlinear optical materials, catalysts, etc. Among them, phthalocyanine complexes have the prospect of being used as photosensitizers in photodynamic therapy (Photodynamic Therapy) Eye-catching. [0003] The so-called photodynamic therapy (or photodynamic therapy), in essence, is the application of the photosensitization reaction of photosensitizers (or photosensitizers) in the medical field. The process of action is to first inject the photosensitizer into the body, and after a period of time (this waiting time is to allow the drug to be relati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00A61L2/08A61P1/02A61P9/10A61P17/00A61P27/02A61P31/04A61P31/12A61P35/00C02F1/30
CPCA61K41/0071A61L2/0076A61L2202/22A61P1/02A61P9/10A61P17/00A61P27/02A61P31/04A61P31/12A61P35/00C02F1/30C02F2303/04C07D487/22
Inventor 黄剑东李兴淑
Owner FUZHOU UNIV
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